Bazı Yeni 1,2,4‐Triazole‐3‐on Türevlerinin Sentezi ve Biyolojik Aktivitelerinin İncelenmesi

Yıl 2018, Cilt: 8 Sayı: 2, 171 - 180, 31.12.2018

Nurhan Gümrükçüoğlu Bahar Bilgin Sökmen

https://doi.org/10.31466/kfbd.481807

Öz

Schiff bazları mükemmel karakteristikliğe, doğal biyolojik maddelerle yapısal benzerliklere ve sentetik esnekliğe sahiptirler. Primer aminlerin aldehidler ile Schiff baz-bimoleküler kondenzasyon ürünleri, organik sentezde değerli ara maddeleri temsil eder. Salisilaldehitden türeyen Schiff bazlarının bitki büyüme düzenleyici, antimikrobiyen veya antimikotik aktivitesi olduğu bildirilmiştir. Bir dizi Schiff bazının kantitatif yapı-antitümör aktivite ilişkisini açıklayan çalışmalarda, salisilaldehitlerden elde edilen ligandlarda en iyi korelasyonun sağlandığı gösterilmiştir. Bu çalışmada substitue amino bileşiklerinin 5-Bromosalisilaldehit ile reaksiyonundan 6 yeni Schiff bazları sentezlendi ve yapıları, spektroskopik verilerle aydınlatıldı. Bu bileşik serisinin biyolojik aktiviteleri değerlendirildi. Sonuçlar, sentezlenen yeni bileşiklerin etkili antioksidan ve antiüreaz aktiviteye sahip olduğunu göstermektedir.

Anahtar Kelimeler

1 2 4‐Triazole‐3‐on, 5-Bromosalisilaldehit, Amino Bileşikleri, Antioksidan Aktivite, Antiüreaz Aktivite

Synthesis of Some New 1,2,4‐Triazole‐3‐one Derivatives and Investigation of Biological Activity

Öz

Schiff bases have excellent characteristics, structural similarities with natural biological agents and synthetic flexibility. Schiff base-bimolecular condensation products with aldehydes of primary amines represent valuable intermediates in organic synthesis. Schiff bases derived from salicylaldehyde have been reported to have plant growth regulator, antimicrobial or antimycotic activity. In studies describing the relationship between quantitative structure-antitumor activity of a series of Schiff bases, Salicyldehydes have been shown to provide the best correlation in the ligands. In this study, 6 new Schiff bases were synthesized from the reaction of the substituted amino compounds with 5-bromosalicylaldehyde and their structures were illuminated spectroscopic data. The biological activities of this compound series were evaluated. The results show that the novel compounds synthesized have effective antioxidant and antiurease activities.

Anahtar Kelimeler

1 2 4‐Triazole‐3‐one, 5-Bromosalicylaldehyde, Amino Compounds, Antioxidant Activity, Antiurease Activity

Kaynakça

• References
• Arnao, M.B., Cano, A., and Acosta, M. (2001). The hydrophilic,and lipophilic contribution to total antioxidant activity. Food Chemistry, 73, 239-244.
• Ashassi-Sorkhabi, H. S., Shabani, B., Aligholipour, B., and Seifzadeh, D. (2006). The effect of some Schiff bases on the corrosion of aluminum in hydrochloric acid solution. Applied Surface Science, 252, 4039-4047.
• Brand-Williams, W., Cuvelier, M. V. and Berset, C. (1995). Use of a Free Radical Method to Evaluated Antioxidant Activity. LWT-Food Science Technology, 26, 25-30.
• Campos, A., Anacona, J. R. and Campos-Vallette, M. M. (1999). Synthesis And Ir Study Of A Zinc(II) Complex Containing A Tetradentate Macrocyclic Schiff Base Ligand: Antifungal Properties. Main Group Metal Chemistry, 22, 283-288.
• Chidananda, N., Poojary, B., Sumangala, V., Kumari, N. S., Shetty, P., Arulmoli, T. (2012). Facile synthesis, characterization and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo-3,4-b][1,3,4]thiadiazoles and 5,6-dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. European Journal of Medicinal Chemistry, 51, 124-136.
• Griendling, K. K., & FitzGerald, G. A. (2003). Oxidative stress and cardiovascular injury: Part I: Basic mechanisms and in vivo monitoring of ROS. Circulation, 108, 1912-1916.
• Gumrukcuoglu, N., Serdar, M., Celik, E., Sevim, A., & Demirbas, N. (2007). Synthesis of Some Novel 3,5-Diaryl-1, 2, 4-Triazole Derivatives and Investigation of Their Antimicrobial Activities. Turkish Journal of Chemistry, 31, 335-348.
• Henen, M. A., El Bialy, S. A. A., Goda, F. E., Nasr, M. N. A., Eisa, H. M. (2012). 1,2,4-Triazolo[4,3-a]quinoxaline: synthesis, antiviral, and antimicrobial activities. Medicinal Chemistry Research, 21, 2368-2378.
• Hernandes, M. M., Mckee, M. L., Keizer, T. S., Yeaswood, B. C. and Atwood, D. A. Six-coordinate aluminium cations: characterization, catalysis, and theory. (2002). Journal Of The Chemical Society, Dalton Transactions, 3, 410-414.
• Imran, M. J., Iqbal, S., Iqbal, S. and Zia-Ul-Haq, M. (2009). Synthesis and Characterization of Antibacterial Metal [Cu (II), Ni (II), Co (II) and Zn (II)] Complexes with Ofloxacin-imines. Journal of the Chemical Society of Pakistan, 31, 69-73.
• Jungreis, E., Thabet, S. (1969). Analytical Applications of Schiff bases. Marcell Dekker, New York.
• Juszkiewicz, A., Zaborska, A., Olech, Z. (2004). A study of the inhibition of jack bean urease by garlic extract. Food Chemistry, 85, 553-558.
• Khalifa, K. M., Maihub, A. A. El-Ajaily, M. M. and Mobain, S. A. (2010). Coordination Trends of 6-Amino-4-hydroxy-2-mercaptopyrimidine Towards Co (II), Ni (II) and Cu (II) Ions. Journal of the Chemical Society of Pakistan, 32, 650-653.
• Lau, K. Y., Mayr, A., Cheung, K. K. (1999). Synthesis of transition metal isocyanide complexes containing hydrogen bonding sites in peripheral locations. Inorganica Chemica Acta, 285, 223-232.
• Lawrence, J. F. and Frei, R. W. (1976). Chemical Derivatization in Chromatography. Elsevier, Amsterdam.
• Li, S., Chen, S., Ma Yu, H. R. and Liu, D. (1999). Investigation on some Schiff bases as HCl corrosioninhibitors for copper. Corrosion Science, 41, 1273-1287.
• Li, Z. Y., Cao, Y., Zhan, P., Pannecouque, C., Balzarini, J., De Clercq, E., Liu, X. Y. (2013). Synthesis and Anti-HIV Evaluation of Novel 1,2,4-triazole Derivatives as Potential Non-nucleoside HIV-1 Reverse Transcriptase Inhibitors Letters in Drug Design & Discovery, 10, 27-34.
• Maliha, B. I., Hussain, Tariq, M. I., and Siddiqui, H. L. (2009). Mechanistic Studies on the Reaction of o-phthalaldehyde (OPTA) with Urea and its N-alkyl/aryl Derivatives. Journal of the Chemical Society of Pakistan, 31: 829-837.
• Maroney, M. J. & Ciurli, S. (2014). Nonredox nickel enzymes. Chemical Review, 114, 4206-4228.
• Modolo, L. V., de Souza, A. X., Horta, L. P., Araujo, D. P., & de Fátima, Â. (2015). An overview on the potential of natural products as ureases inhibitors: A review. Journal of Advanced Research, 6, 35–44.
• Naz, N. and Iqbal, M. Z. (2009). Synthesis, Spectroscopic and Biological Studies of Transition Metal Complexes of Novel Schiff Bases Derived from Amoxicillin and Sugars. Journal of the Chemical Society of Pakistan, 31, 440-446.
• Olie, G. H. and Olive, S. (1984). The Chemistry of The Catalyzes Hydrogenation of Carbon Monoxide. Springer, Berlin.
• Oyaizu, M.( 1986). Studies on products of browning reactions: Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44, 307–315.
• Patai, S. (1970). The Chemistry of the Carbon-Nitrogen Double Bond. J.Wiley & Sons, London.
• Rice-Evans, C. A., Diplock, A. T. (1991). Techniques in Free Radical Research, Elsevier, Amsterdam, pp. 291.
• Quan, Z., Chen, S. and Li, Y. (2001). Protection of copper corrosion by modification of self-assembled films of Schiff bases with alkanethiol. Corrosion Science, 43, 1071-1080.
• Sari, N., Arslan, S., Logoglu, E. and Sakiyan, I. (2003). Antibacterial activities of some Amino acid Schiff bases. Gujarat Council on Science, 16, 283-288.
• Shawali, A. S., Harb, N. M. S. and Badahdah, K. O. (1985). A study of tautomerism in diazonium coupling products of 4-hydroxycoumarin. Journal Heterocylic Chemistry, 22, 1397-1403.
• Sheo, L. B. U. (2012). Urease Inhibitor: A review. Indian Journal of Biotechnology, 11, 381-388.
• Sogawa, S., Nihro, Y., Ueda, H., . Miki, T., Matsomota, H., Satoh, T. (1994). Protective effects of hydroxychalcones on free radical-induced cell damage. Biological and Pharmaceutical Bulletin, 17, 251–256.
• Spichiger-Keller, U. (1998). Chemical Sesors and Biosensors for Medical and Biological Applications. Wiley-VCH, Weinheim.
• Valcarcel, M. and Laque de Castro, M. D. (1994). Flow-Throgh Biochemical Sensors. Elsevier, Amsterdam.
• Van Slyke, D. D. and Archibald, R. M. (1944). Manometric, Titrimetric and Colometric Methods for Measurements of Urease Activity. Journal of Biological Chemistry, 154, 623-642.
• Verma, M., Pandeya, S. N., Singh, K. N., Stabler, J. P. (2004). Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica Hungarica, 54, 49-56.
• Williams, D. R. (1972). Metals, ligands and cancer. Chemical Reviews, 72, 203-213.